1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{3-(hydroxymethyl)-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamide

HRID 230594

Reaktionsgleichung

Reaktionsgleichung von HRID 230594
Cl.[NH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:7]([CH2:16][OH:17])[CH:6]=1)[CH3:4].[C:18]([C:22]1[C:32]([F:33])=[CH:31][C:25]([O:26][CH2:27][C:28](O)=[O:29])=[CH:24][C:23]=1[F:34])([CH3:21])([CH3:20])[CH3:19].CN(C)CCCN=C=NCC>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:18]([C:22]1[C:23]([F:34])=[CH:24][C:25]([O:26][CH2:27][C:28]([NH:2][C@@H:3]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:7]([CH2:16][OH:17])[CH:6]=2)[CH3:4])=[O:29])=[CH:31][C:32]=1[F:33])([CH3:21])([CH3:19])[CH3:20]

Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68804307N-[4-[(1R)-1-aminoethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide hydrochlorideHCID 68804332(4-tert-Butyl-3,5-difluorophenoxy)acetic acid

Produkt 1

HCID 577629242-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{3-(hydroxymethyl)-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamideAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-[4-[(1R)-1-aminoethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide hydrochloride (40 mg, 0.14 mmol) in N,N-dimethylformamide (DMF) (2 ml), (4-tert-butyl-3,5-difluorophenoxy)acetic acid (34 mg, 0.14 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (40 mg), and 4-dimethylaminopyridine (DMAP) (0.5 mg, 0.004 mmol) were added. The solution was stirred at room temperature for 16 hours and then partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered, and evaporated. The residue obtained was purified by silica gel column chromatography, eluting with methylene chloride/ethylacetate (1:1), to give 2-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{3-(hydroxymethyl)-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamide (24 mg, 36%).

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography
  7. washeluting with methylene chloride/ethylacetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5d2e081b29804d5292c06fcfc514c624
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566739B2

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